(4-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenylethynyl)phenyl)methylamine | 937701-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenylethynyl)phenyl)methylamine
• 英文别名: 4-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)-N-methylaniline；4-[2-[4-[2-[2-(2-fluoroethoxy)ethoxy]ethoxy]phenyl]ethynyl]-N-methylaniline
• CAS: 937701-36-5
• 化学式: C₂₁H₂₄FNO₃
• 分子量: 357.425
• InChiKey: ZPLMXEYKAUEZGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenylethynyl)phenyl)methylamine 在 [RuHCl(CO)(PPh₃)₃] 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以76%的产率得到(E)-4-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)styryl)-N-methylaniline
  参考文献：
  名称：

  两室反应器中直接反式选择性钌催化的炔烃还原和连续流动

  摘要：

  据报道，使用可商购的氢化钌配合物，在低氢压力和低反应温度下有效的炔烃的反式选择性氢化。可以耐受各种官能团的发达反应条件是在两室设置下利用异位产生的氢气进行的。反应设置非常适合氘标记。的反式-选择性氢化外推至一个转移氢化协议，采用连续流动仅为10分钟的保留时间的填充床固定化钌氢化催化剂。

  DOI：

  10.1021/acscatal.6b01045
• 作为产物：
  描述：

  1-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-4-iodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide ammonium hydroxide 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 (4-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenylethynyl)phenyl)methylamine
  参考文献：
  名称：

  New Diphenylacetylenes as Probes for Positron Emission Tomographic Imaging of Amyloid Plaques

  摘要：

  A series of F-18 fluoropegylated diphenylacetylenes as probes for binding to A beta plaques were successfully prepared. These relatively rigid acetylenes, 12a, 12b, 14a, and 14b, displayed high binding affinities in postmortem AD brain homogenates (K-i ranging from 1.2 to 2.9 nM). In vivo biodistribution in normal mice exhibited excellent initial brain penetrations (4.42, 4.55, 5.41, and 6.78% dose/g at 2 min for [F-18]12a, 12b, 14a, and 14b, respectively). [F-18]12b and [F-18]14b, with a longer fluoropegylated unit, that is, n = 3, showed faster brain washout at 30 min postinjection (0.42 and 1.57% dose/g) as compared to the shorter fluoropegylated chain ligands, that is, [F-18]12a and [F-18]14a(1.03 and 3.69% dose/g). Autoradiography and homogenate binding confirmed the high binding signal due to A beta plaques. These preliminary results suggest that the novel diphenylacetylenes may be potentially useful for imaging of A beta plaques in the brain of patients with Alzheimer's disease.

  DOI：

  10.1021/jm070090j

文献信息

• Acetylene Derivatives And Their Use For Binding And Imaging Amyloid Plaques
  申请人：Kung Hank F.

  公开号：US20080166299A1

  公开（公告）日：2008-07-10

  The invention relates to radiolabeled compounds and their use in methods of imaging amyloid deposits, as well as to methods of their manufacture. The invention also relates to compounds for inhibiting the aggregation of amyloid proteins that form amyloid deposits, methods for delivering therapeutic agents to amyloid deposits, as well as methods of making compounds that inhibit the aggregation of amyloid proteins.

  这项发明涉及放射标记化合物及其在成像淀粉样沉积方法中的应用，以及它们的制造方法。该发明还涉及用于抑制形成淀粉样沉积的淀粉蛋白聚集的化合物，将治疗剂传递至淀粉样沉积的方法，以及制造抑制淀粉蛋白聚集的化合物的方法。
• A Versatile Approach to β-Amyloid Fibril-Binding Compounds Exploiting the Shirakawa/Hayashi Protocol for <i>trans</i>-Alkene Synthesis
  作者：Tri H. V. Huynh、Mette Louise H. Mantel、Katrine Mikkelsen、Anders T. Lindhardt、Niels Chr. Nielsen、Daniel Otzen、Troels Skrydstrup

  DOI：10.1021/ol8029593

  日期：2009.2.19

  Application of the Sonogashira coupling reaction followed by a trans-selective alkyne reduction proved highly adaptable for the efficient synthesis of a class of beta-amyloid fibril binding compounds possessing a styrylbenzene motif such as FSB, an FSB dimer, and F-19-BAY94-9172.
• PET MONITORING OF A-BETA-DIRECTED IMMUNOTHERAPY
  申请人：Black Ronald

  公开号：US20130084245A1

  公开（公告）日：2013-04-04

  The present invention provides methods of monitoring Aβ-directed immunotherapy. The methods involve administering a PET ligand that binds to amyloid deposits and detecting the PET ligand in the brain to provide an indication of the level and/or distribution of amyloid deposits. Surprisingly, the data in the present application show that a statistically significant reduction in amyloid deposits occurs early and consistently among patients following initiation of treatment before statistically significant effects of most if not all other markers are detectable. In consequence, the present methods allow early detection of whether a patient is responding to the Aβ-directed immunotherapy and if necessary adjustment of the immunotherapy regime.
• New Diphenylacetylenes as Probes for Positron Emission Tomographic Imaging of Amyloid Plaques
  作者：Rajesh Chandra、Shunichi Oya、Mei-Ping Kung、Catherine Hou、Lee-Way Jin、Hank F. Kung

  DOI：10.1021/jm070090j

  日期：2007.5.1

  A series of F-18 fluoropegylated diphenylacetylenes as probes for binding to A beta plaques were successfully prepared. These relatively rigid acetylenes, 12a, 12b, 14a, and 14b, displayed high binding affinities in postmortem AD brain homogenates (K-i ranging from 1.2 to 2.9 nM). In vivo biodistribution in normal mice exhibited excellent initial brain penetrations (4.42, 4.55, 5.41, and 6.78% dose/g at 2 min for [F-18]12a, 12b, 14a, and 14b, respectively). [F-18]12b and [F-18]14b, with a longer fluoropegylated unit, that is, n = 3, showed faster brain washout at 30 min postinjection (0.42 and 1.57% dose/g) as compared to the shorter fluoropegylated chain ligands, that is, [F-18]12a and [F-18]14a(1.03 and 3.69% dose/g). Autoradiography and homogenate binding confirmed the high binding signal due to A beta plaques. These preliminary results suggest that the novel diphenylacetylenes may be potentially useful for imaging of A beta plaques in the brain of patients with Alzheimer's disease.
• Direct <i>trans</i>-Selective Ruthenium-Catalyzed Reduction of Alkynes in Two-Chamber Reactors and Continuous Flow
  作者：Karoline T. Neumann、Sebastian Klimczyk、Mia N. Burhardt、Benny Bang-Andersen、Troels Skrydstrup、Anders T. Lindhardt

  DOI：10.1021/acscatal.6b01045

  日期：2016.7.1

  efficient trans-selective hydrogenation of alkynes under low hydrogen pressure and low reaction temperatures is reported, applying a commercially available ruthenium hydride complex. The developed reaction conditions, which tolerate a variety of functional groups, are carried out in a two-chamber setup with ex situ generated hydrogen. The reaction setup is highly suitable for deuterium labeling. The trans-selective

  据报道，使用可商购的氢化钌配合物，在低氢压力和低反应温度下有效的炔烃的反式选择性氢化。可以耐受各种官能团的发达反应条件是在两室设置下利用异位产生的氢气进行的。反应设置非常适合氘标记。的反式-选择性氢化外推至一个转移氢化协议，采用连续流动仅为10分钟的保留时间的填充床固定化钌氢化催化剂。